IL27374A - Preparation of organic boron derivatives - Google Patents
Preparation of organic boron derivativesInfo
- Publication number
- IL27374A IL27374A IL27374A IL2737467A IL27374A IL 27374 A IL27374 A IL 27374A IL 27374 A IL27374 A IL 27374A IL 2737467 A IL2737467 A IL 2737467A IL 27374 A IL27374 A IL 27374A
- Authority
- IL
- Israel
- Prior art keywords
- boron
- general formula
- preparation
- organic
- ether
- Prior art date
Links
- 150000001638 boron Chemical class 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 16
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 15
- 150000001639 boron compounds Chemical class 0.000 claims description 14
- 229910052749 magnesium Inorganic materials 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 239000000725 suspension Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Chemical group 0.000 claims description 2
- 230000004048 modification Effects 0.000 claims description 2
- 238000012986 modification Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- KVNYFPKFSJIPBJ-UHFFFAOYSA-N 1,2-diethylbenzene Chemical compound CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 26
- 229910052796 boron Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 229960004132 diethyl ether Drugs 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- -1 boron halide Chemical class 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 229960002645 boric acid Drugs 0.000 description 2
- 235000010338 boric acid Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229960003750 ethyl chloride Drugs 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- UNFUYWDGSFDHCW-UHFFFAOYSA-N monochlorocyclohexane Chemical compound ClC1CCCCC1 UNFUYWDGSFDHCW-UHFFFAOYSA-N 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- RKLSGKOUKYOIRM-UHFFFAOYSA-N butylboron Chemical compound [B]CCCC RKLSGKOUKYOIRM-UHFFFAOYSA-N 0.000 description 1
- MEYBRJQJBOJHPQ-UHFFFAOYSA-N chlorobenzene;chloromethylbenzene Chemical compound ClC1=CC=CC=C1.ClCC1=CC=CC=C1 MEYBRJQJBOJHPQ-UHFFFAOYSA-N 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
preparation of organic boron derivatives This invention relates to the preparation of organic boron derivatives having direct bonds between carbon and boron and the general formula in which represents an alkyl cycloalkyl or aralkyl Organic boron compounds of the type can be prepared by reactin a suitable reagent of the in which is as defined above and X represents a halogen atom such as a bromine or iodine with a boron compound such as a boron halide or an alkyl or with the reaction product of either of these with In this the reagent must first be prepared by a separate and then it is reacted with the boron This operating procedure has the considerable drawbacks and disadvantages that it requires a very long reactio and in the separate preparatio of the reagent it is essential to use large quantities of it is necessary to adopt stringent precautionary measures because of the presence of the highly inflammable Also this tion requires the use of expensive boron some of which could not readily be available on the The has been made with a view to overcoming or reducing these drawbacks and According to the invention there is provided a process for the preparation of organic boron compounds having direct boro carbon bonds and the general in which R represents an cycloalkyl or aralkyl grou comprising reacting a compound having the general RX in which represents an group with a linear or branched chain and containing from 2 to 6 carbon or a phenyl or a substituted phenyl and n is 1 or with a suspension of magnesium in an inert organic hydrocarbon solvent in the sence of a catalytic amount of According to a preferred embodiment of the the compound having the general formula in which R is as above and X represents a halogen atom such as a bromine or iodine radical and a boron derivative are at a temperature of from 80 to with a suspension of magnesium in an organic hydrocarbon solvent in the presence of a catalytic amount of an These processes in accordance with the invention have the advantages that they are effected in a single reaction stage and also the boron derivatives used are relatively cheap and easy to There is a wide range of arylalkyl and cycloalkyl halides which can be used as the compound represented by the formula Preferred compounds for the halogenated derivatives of aliphatic hydrocarbons with a straight or branched chain containing from 2 to 6 carbon the hexyl halides and the aryl and arylalkyl halogenated derivatives such as chlorobenzene benzylchloride and As a modification of the a mixture of two or more compounds represented by RX can be used and then the organic boron compound may have at least one group represented by R different from the other groups represented by The boron derivative is one having the general A in which represents an radical having a straight or branched chain and from 2 to 6 carbon atoms or a pheny or substituted phenyl and n is 1 or but is preferably less than Such derivatives can be prepared from an alcohol or phenol and orthoboric acid according to the method described Israel in our Application According to the method described in that application the organic boron derivatives with the above which are generally known as polyborates or are prepared by reacting an alcohol or a phenol with partially dehydrated boric the dehydration of the acid and its subsequent tion in the same apparatus being effected in an inert organic liquid The boron derivative is obtained in the form of a solu tion or suspension in the inert organic liquid medium when this inert organic liquid is a his solution or pension can be advantageously used at the source of boron in the process according to the present When compared with the previously used boron compounds such as the boron the esters of boric acid and the reaction products of these latter with boric anhydrides the compounds of the prepared as above have the advantage that they far less expensive and are easily prepared in high yields from boron compounds such as which is readily obtainable at prices far lower than the prices of boron halides of the boric simply adding the metal to an inert hydrocarbon solvent presence of a catalytic amount of an Suitable inert organic solvents which be used for all those which do not boil under the reaction temperature which is normally higher than and is preferably from 80 to By way of illustration preferred solvents are ethylbenzene ethylpropylbenzene propylbenzene and or Particularly suitable solvents are those inert organic liquids that may act as solvents or as suspending agents for the boron compounds having the formula such as for instance diethylbenzene and The magnesium metal is but not activated with very small quantities of ethyl before In the process according to the invention ether is used in very small It has been surprisingly and this constitutes an important advantage of this that traces of ether are quite sufficient to promote the formation of organic boron compounds having the formula in industrially acceptable Good results are obtained with an ether in such an amount that the ratio of ether to compound having the formula is from to The ether which can be used may be selected from a wide Particularly suitable proved to be diethyl ether and di n but l In the process according to this invention the ratios between the various compounds by lead to the organic boron compound having the and having direct links may vary within very wide According to a preferred form of the magnesi metal ether in catalytic quantities and an organi hydrocarbon liquid instance are placed in a After heating to a temperature of about the type compound and a boron type compound are added in the form of a solution or a suspension in an organic inert hydrocarbon but not the same as used for the preparation of the magnesium By properly regulating the the temperature of the reaction mixture can be maintained between 80 and Then after reaction the organic boron derivative can be obtained from the reaction mixture by The invention will now be illustrated by following t g of magnesium shavings were placed in a 4 1 fitted with a a a gas inlet pipe and a dipped dripping The reactor was flushed with a niirogen and then g of diethyl 5 ml of ethyl iodide and ml of diethylbenzene mixture of the three were introduced through the The mixture was stirred and heated to upon a mixture of 290 g of ethyl chloride and 450 ml of a solution in diethylbenzene of ethyl polyborate slowly dripped into the Because of the reaction of the two the temperature of the reaction mixture tended Therefore the rate of addition was regulated so as to keep the temperature around Once the mixing of the reactants had been complete the reaction mass was kept for a further 1 hour at the of The reaction mixture was then distilled under nitrogen current and the fraction boiling at was g of were the yield being calculated with respect to the starting EXAMPLE 2 Using a reactor similar to the one described in Example a suspension of 108 g of magnesium in 1200 ml of diethylbenzene was made in the Also of ether and 5 ml of ethyl iodide were After the suspension had been heated to a temperature of a mixture 490 g of and 450 ml of a solution of ethyl similar to that of the preceding was slowly dripped into the mixture with The addition was effected in such a way as to keep the temperature of the reaction mass between 100 and 1 Once all the reactants had been the reaction mixture was kept for a further hour at a temperature of Then the mixture was distilled under a slow nitrogen current and the fraction boiling at was The yield of was calculated with respect to the starting EXAMPLE 5 dripping 21 kg of raw crystalline magnesium 250 litres of diethylbenzene and 20 litres of diethyl ether were This mixture was then heated with stirring to a temperature of at a rate of 50 to 60 a mixture of 681 of ethyl chloride and 1 of a solution in diethylbenzene of ethyl polyborate having a boron content of was fed into the The addition of the mixture was effected at such a rate as tomaintaln the temperature at between 90 and After the addition of the the reaction mixture was then Kept for another hour at a temperature of from 90 to The reaction mixture was then distilled under a light nitrogen current and the fraction boiling at 94 to 96o G was Kg of were corresponding to a with respect to the starting of EXAMPLE 4 Into a 1000 ml similar to the one described in Example a mixture of 18 g of magnesium shavings g of diethyl ether 1 ml of ethyl iodide and 200 ml of diethylbenzene was The mixture was heated with stirring to and then a mixture of 118 g of and g of a solution in diethylbenzene of ethyl polyborate a boron content of by weight and a ratio of B to of was slowly dripped into the was obtained in a yield of 68 with respect to the starting EXAMPLE 5 Following the operational procedure of Example 4 and using the same 1 ml of ethyl g of diethyl a mixture of g of and g of a ratio of B to of were dripped into a suspension of 18 g of magnesium in 200 ml of Keeping the reaction temperature at about butylboron was obtained in a yield of with respect to the starting 6 Following the operation procedure of Example 4 and using the same a mixture of 89 g of chlorocyclohexane and ml of a solution in diethylbenzene of ethyl polyborate ratio equa to was reacted with a suspension of 18 g of magnesium in 200 ml of g of diethyl ether and 1 ml of ethyl The temperature was maintained at about during the Borotricyclohexane was formed with a yield of with respect to the starting EXAMPLE 7 Following the operational procedure and using the same reactants as in Example except that g of benzyl bromide instead of chlorocyclohexane was the action was The reaction was effected at a temperature of between 160 and The yield of was with respect to the 8 By operating as in the preceding g of magnesium in a suspension of 1200 ml of diethylbenzene which also contained 7 g diethyl ether and 5 ml of ethyl were reacted with 490 g of ethylbromide and 450 ml of a solution of ethyl polyborate similar to that of Example at a temperature of Triethyl boron was formed with a yield calculated on the starting boron of EXAMPLE 9 Following the procedure of the preceding Examples 18 g of magnesium suspended in 200 of diethylbenzene and which also contained g of diethylether and 1 ml of were reacted with 82 g of ethylbromide and a solution in diethylbenzene of butylpolyborate having a titre in boron of by weight and a ratio of B to of The reaction temperature was kept between 100 and was obtained with a yield of calculated with respect to the starting EXAMPLE Following the procedure of the preceding 18 g of magnesium suspended in 200 ml of diethylbenzene which al30 contained g of diethylether and 1 ml of were reacted with 82 g of ethylbromide and a solution in benzene of phenyl polyborate a titre in boron of and a ratio of B to of The reactio temperature was between 100 and Triethylboron was obtained in a yield of with EXAMPLE Example 10 was repeated using instead as the boron derivative ethoxy boroxine form of a solution of 18 g of boron compound in 100 ml of The reaction temperature was kept between 100 and Triethylboron was obtained in a yield of with respect to the starting 12 insufficientOCRQuality
Claims (9)
1. A process for the preparation of organic boron compounds having direct boron-carbon bonds and the general formula: BR, 3 in which R represents an alkyl, aryl, cycloalkyl or aralkyl group, comprising reacting a compound having the general formula: RX in which R is as above and X represents a chlorine, bromine or iodine atom, and a boron derivative having the general formula: ( '0)3B.(B203)n in which R* represents an alkyl group with a linear or branched chain and containing from 2 to 6 carbon atoms, or a phenyl or a substituted phenyl group, and n is 1 or larger, with a suspension of magnesium in an inert organic hydrocarbon solvent in the presence of a catalytic amount of an ether.
2. A process as claimed in Claim 1 in which the reaction is effected in the presence of an ether in such an amount that the molar ratio of ether to the compound having the formula RX is from 0.01 to 0.5.
3. A process as claimed in Claim 1 or 2 which is effected at a temperature of from 80 to 180°C.
4. A process as claimed in any preceding Claim in which a small quantity of ethyl iodide is added to the suspension of magnesium before the reaction.
5. A process as claimed in any preceding Claim in which n is less than 2.
6. A process as claimed in any preceding Claim in which - 13 - 27374/2 in Claim 1 of British Patent Serial No. 1156980.
7. A modification of the process claimed in any preceding claim for the preparation of organic boron compounds having direct boron-carbon bonds and the general formula BH^, in which at least one group represented by R is different from the other groups represented by R, comprising using a mixture of two or more different compounds having the general formula RX.
8. A process according to Claim 1 for the preparation of organic boron compounds having direct boron-carbon bonds and the general formula BR-jf substantially as herein described with reference to any Example.
9. An organic boron compound when prepared by a process as claimed in any preceding claim. mz
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT229666 | 1966-02-03 | ||
| IT1409166 | 1966-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL27374A true IL27374A (en) | 1970-11-30 |
Family
ID=26325233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL27374A IL27374A (en) | 1966-02-03 | 1967-02-01 | Preparation of organic boron derivatives |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US3502729A (en) |
| BE (1) | BE693650A (en) |
| CH (1) | CH477477A (en) |
| DE (1) | DE1618645A1 (en) |
| ES (1) | ES336839A1 (en) |
| FR (1) | FR1517893A (en) |
| GB (1) | GB1169603A (en) |
| IL (1) | IL27374A (en) |
| NL (1) | NL6701488A (en) |
| SE (1) | SE331995B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109232224B (en) * | 2018-10-26 | 2021-02-19 | 西安凯立新材料股份有限公司 | Preparation method of 2-phenylpropionic acid |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2880243A (en) * | 1956-05-09 | 1959-03-31 | Olin Mathieson | Manufacture of trisubstituted boranes |
| US3090801A (en) * | 1956-07-06 | 1963-05-21 | American Potash & Chem Corp | Aryl polyboronic acids and esters and process for their preparation |
| US2939885A (en) * | 1957-07-29 | 1960-06-07 | Olin Mathieson | Production of trialkylboranes |
| US2862952A (en) * | 1957-08-26 | 1958-12-02 | American Cyanamid Co | Method of preparing b-hydrocarbonsubstituted boron compounds |
| US3345418A (en) * | 1957-08-29 | 1967-10-03 | Herbert C Brown | Catalytic process for preparing organoboron compounds from diborane |
| US3100181A (en) * | 1961-02-16 | 1963-08-06 | Nalco Chemical Co | Preparation of organoboranes |
| US3405179A (en) * | 1963-11-08 | 1968-10-08 | M & T Chemicals Inc | Method of preparing arylborane compounds |
| NL6415119A (en) * | 1964-01-02 | 1965-07-05 |
-
1967
- 1967-01-31 NL NL6701488A patent/NL6701488A/xx unknown
- 1967-02-01 DE DE19671618645 patent/DE1618645A1/en active Pending
- 1967-02-01 ES ES336839A patent/ES336839A1/en not_active Expired
- 1967-02-01 IL IL27374A patent/IL27374A/en unknown
- 1967-02-01 FR FR93298A patent/FR1517893A/en not_active Expired
- 1967-02-02 US US613416A patent/US3502729A/en not_active Expired - Lifetime
- 1967-02-02 SE SE01530/67A patent/SE331995B/xx unknown
- 1967-02-02 GB GB5185/67A patent/GB1169603A/en not_active Expired
- 1967-02-02 CH CH151867A patent/CH477477A/en not_active IP Right Cessation
- 1967-02-03 BE BE693650D patent/BE693650A/xx unknown
-
1969
- 1969-09-30 US US862464A patent/US3594426A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES336839A1 (en) | 1968-02-16 |
| BE693650A (en) | 1967-08-03 |
| DE1618645A1 (en) | 1971-04-01 |
| GB1169603A (en) | 1969-11-05 |
| US3594426A (en) | 1971-07-20 |
| US3502729A (en) | 1970-03-24 |
| SE331995B (en) | 1971-01-25 |
| FR1517893A (en) | 1968-03-22 |
| NL6701488A (en) | 1967-08-04 |
| CH477477A (en) | 1969-08-31 |
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